Hydrochloric Acid → 3-(4-Bromobenzoyl)propionic acid

HRID 489217Notes

Reaction equation

HRID 489217 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1(=[O:11])[O:10][C:8](=[O:9])[CH2:7][CH2:6]1.[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>C(Cl)Cl>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:5](=[O:11])[CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 7961BromobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 806463-(4-Bromobenzoyl)propionic acidYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

AlCl3 (128.8 g, 0.97 mol) was added by portions within 20 min to a suspension of succinic anhydride (44.3 g, 0.44 mol) and bromobenzene (100 ml, 0.99 mol) in DCM (500 ml) while the reaction flask was cooled in a water bath. After 1 h30 min at RT, the reaction mixture was refluxed for 2 h. After cooling, the reaction medium was slowly poured into a mixture of ice (1.5 l) and concentrated HCl (100 ml). The precipitate was washed twice with water, with isopropanol, and finally with pentane. After drying 4-(4-bromophenyl)-4-oxobutyric acid was obtained as an off-white solid (86.4 g, mp=148° C.). 1H NMR (CDCl3): 7.85 (2H, d, J=8.5 Hz), 7.62 (2H, d, J=8.5 Hz), 3.28 (2H, t, J=6.5 Hz), 2.82 (2H, t, J=6.5 Hz).

Workup

  1. temperaturewas cooled in a water bath
  2. temperatureAfter cooling
  3. washThe precipitate was washed twice with water, with isopropanol
  4. dry with materialAfter drying 4-(4-bromophenyl)-4-oxobutyric acid

Sources & evidence

ORD record
ord-ae59442be2b04ff2be8a0e93e6257064
Source dataset
uspto-grants-2005_12
Patent number
US06977267B2

Reaction notes

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